1-Ethyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid → 7-(3-Ethenyl-1-piperazinyl)-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 2165678Notes

Reaction equation

[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:14])=[C:10](F)[CH:11]=2)[C:6](=[O:15])[C:5]([C:16]([OH:18])=[O:17])=[CH:4]1)[CH3:2].[CH:19]([CH:21]1[NH:26][CH2:25][CH2:24][NH:23][CH2:22]1)=[CH2:20]>N1C=CC=CC=1>[CH:19]([CH:21]1[NH:26][CH2:25][CH2:24][N:23]([C:10]2[CH:11]=[C:12]3[C:7]([C:6](=[O:15])[C:5]([C:16]([OH:18])=[O:17])=[CH:4][N:3]3[CH2:1][CH3:2])=[CH:8][C:9]=2[F:14])[CH2:22]1)=[CH2:20]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 1.2 g of 1-ethyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 1.9 g of 3-ethenylpiperazine and 15 ml of pyridine is heated at 100° C. in a pressure bottle for 3 hours, then cooled and evaporated. The residue is purified by silica gel flash chromatography, eluting with chloroform:methanol:water:triethylamine (9:0.5:0.02:0.02), giving 200 mg of the desired product.

Workup

temperaturecooled
customevaporated
customThe residue is purified by silica gel flash chromatography
washeluting with chloroform:methanol:water:triethylamine (9:0.5:0.02:0.02)

Sources & evidence

ORD record: ord-01831471bd5743fba5734de0fb757210
Source dataset: uspto-grants-1990_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04940710

Reaction notes

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